Method of obtaining an azo compound from phenyl-diazo-amino-alpha-monamino-pyridine



Patented Aug. 25,1931

- UNITED ATEs PATENT; omen,

IWAN OSTROMISLENSKY, OFNEW'YORK, N." Y., ASSIGNOR TO THE PYRIDIUM GOBPO- RATION, on NEW YORK,

N. Y., A CORPORATION NEW YORK METHOD or OBTAINING nAzo COMPOUND FROM PHENYL-nIAZo-AMIno-ALrHA- I MONAMlNo-PYRlDINE' No Drawing.. Original application filed September 23, 1927, SerialNo. 221,628. Divided and this application' filed June 9, 1928. Serial No. 284,282.

' This invention is an improvement in methods of obtaining a substance composed of dines. I One of the primaryobjects of the invention is the provision of a method for preparing the substance, that is, phenyl-diazo-aminoalpha-monamino-pyridine hydrochloride,

that is, from the substanceforming the sub 1 ject matter of my copendingapplication serial No. 221,628, filed. on Sept. 23, 1927 of which the application is a division.

This substance is obtainediby coupling 'phenyl-diazonium salt with alpha-alphadiamino-pyridine, under certain conditions,

by means of which there is obtained phenyldiazo-amido-alpha-monamino pyridine. The 1, product is obtained not only when coupling is performed in an aqueous medium acidified with an organic acid, such as acetic acid, but likewise when an insuflicient amount of mineral acid, such as hydrochloric acid, is used. The compound appears infine, prismatic, yellowish brown crystals, and dissolves'very easily in aniline and in'pyridine. It comprises in its structure the following grouping: i

For this purpose 1t 1s suflicient to boil the given hydrochloride with 'puredistilled wa ter for from one-half toftWo hours. In this time the original hydrochloride dissolves in water and are quantitatively converted into p phenyl-azo-alpha-alpha diamino pyridine phenyl-azo-alpha-alpha-diamino-pyrihydrochloride, in accordance with the following reaction nzN N NH,

purpose, it is sufiicient to boil it with distilled 2 water with a reflux condenser.

The Y phenyl-d1azo-am1 o-alpha monamino-pyridine hydrochloride described above pyridine hydrochloride, inboiling water,

is easily converted into phenyl-azo-diamino and by the stomach juices when ingested I the mouth.

What is claimed as new is 1. The method of obtaining phenyl-azodiamino-pyridine' hydrochloride, which consists in boiling the hydrochloride of phenyldiazo-amino-alpha-monamino-pyridine with a solvent.

diamino pyridine hydrochloride, which, condiazo-amino-alpha-monainino-pyridine with water.

2. The method of obtaining phenyl-azo-' 3. The method of'obtaining phenyl-azodiamino-pyridine hydrochloride, which consists in reacting phenyl-diazonium salt with alpha alpha-diamino-pyridine in a weakly acidified aqueous medium, and afterwards boiling the product in a solvent.

Signed at New York and State of New York this 7th day of June A. D. 1928. I

v IWVAN OSTROMISL'ENSKY.

New York city, in the county of 

